E-1-chloro-3,3,3-trifluoropropene (E-1233zd) can be produced by fluorinating 1,1,1,3,3-pentachloropropane (240fa). For example, documents U.S. Pat. Nos. 8,436,217 and 8,426,656 describe the liquid phase fluorination of 240fa to E-1233zd, with the presence of suitable catalysts such as TiCl4 or a combination of TiCl4 and SbCl5.
FR 2768727 also explains that the fluorination of 240fa or 1230za can be completed with a catalyst such as TiCl4.
US 2010/0191025 and U.S. Pat. No. 6,166,274 also describe the use of a catalyst for liquid phase fluorination of 1230za, with a view to obtaining E-1233zd: an ionic liquid based catalyst in the first document and a triflic or trifluoroacetic acid in the second document. US 2012/0059199 describes the liquid phase fluorination of 240fa without a catalyst. This document explains that a drawback to the non-catalyzed liquid phase process is the low reaction conversion rate. Several series reactors are therefore necessary to increase the overall conversion rate, each reactor contributes to improving the conversion rate.
US 2013/0211154 describes the use of increased reaction pressure as well as an agitated fluorination reactor to increase the rate of conversion in a non-catalyzed liquid phase 240fa process. Nevertheless, there is no indication of the conversion rate.
U.S. Pat. No. 6,987,206 describes the possibility of obtaining E-1233zd from 1230za as an intermediary, without indicating operational conditions.
An example of the non-catalyzed liquid phase fluorination reaction for 1230za is provided in U.S. Pat. No. 5,616,819. The pressure used is 200 psi (14 bar) and leads to the formation of oligomers, despite the shortness of the batch test.
U.S. Pat. No. 5,877,359 presents the non-catalyzed liquid phase fluorination of 1230za. The examples show that a very high molar ratio of 166 was used to obtain a full conversion on a short test batch. When the molar ratio falls to 12.6, a pressure of 600 psig (42 bar) is applied. On the other hand, the operational conditions of an extrapolable continuous process are not defined: molar ratio HF/1230za, reflux temperature, kind of by-products to be distilled. Nor are the productivity or stability over time of a process which is based on this reaction described.
There is still a need to develop a new continuous production process which can be extrapolated to E-1233zd without restrictive operational conditions (such as excessive pressure), high molar ratio or agitation in the fluorination reactor.